1,4-Dioxane → HCID 86711374, compound

HRID 532926Notes

Reaction equation

HRID 532926 reaction equation
Cl[C:2]1[C:11]2[CH2:10][CH2:9][N:8]3[C:12](=[O:18])[CH2:13][NH:14][C:15](=[O:17])[CH2:16][CH:7]3[C:6]=2[N:5]=[CH:4][CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([Sn](CCCC)(CCCC)CCCC)=[CH:22][N:21]=1.O1CCOCC1>>[F:19][C:20]1[N:21]=[CH:22][C:23]([C:2]2[C:11]3[CH2:10][CH2:9][N:8]4[C:12](=[O:18])[CH2:13][NH:14][C:15](=[O:17])[CH2:16][CH:7]4[C:6]=3[N:5]=[CH:4][CH:3]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 164271002-Fluoro-5-(tributylstannyl)pyridineHCID 86711373HCID 86711373, compound

Product 1

HCID 86711374HCID 86711374, compoundYield 39.2%

Conditions

Temperature
150 °C

Procedure

94-10. To a degassed solution of 4-chloro-5,6,9,10,12,12a-hexahydro-[1,4]diazepino[1,7-h][1,7]naphthyridine-8,11-dione (66 mg, 0.25 mmol) and 2-fluoro-5-(tributylstannyl)pyridine (120 mg, 0.31 mmol) in dioxane (2 mL) Pd(PPh3)4 (15 mg, 0.012 mmol) was added and the mixture was heated in the microwave at 150° C. for 5 h. The solvent was removed under reduced pressure. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent: from 2% MeOH in AcOEt to 20% MeOH in AcOEt in 21 min) to yield the title compound as a beige solid (32 mg). UPLC-MS: MS 327.2 (M+H+); UPLC rt 0.58 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent: from 2% MeOH in AcOEt to 20% MeOH in AcOEt in 21 min)

Sources & evidence

ORD record
ord-504435ed17424b858b9e09fd50bf36ed
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

Loading…